Michigan Rep. John Dingell is set to become the longest-serving member of Congress in history on Friday, and during his 57 years on Capitol Hill, he’s served under 11 presidents and 11 speakers of the House.

But according to the dean of the House, President Obama and his staff haven’t grasped the interworking and interplay necessary for success between the White House and Congress.

“He’s a good man, and he will go down in history as a good president,” Dingell said in a wide-ranging interview with The Daily Rundown’s Chuck Todd in the longtime Democrat’s Capitol Hill office.

But, Dingell said, the president’s inexperience coupled with ambition after just four years in the Senate have shown as the White House has battled with lawmakers and scrambled to contain scandals.

“I think he had the smallest rolodex–ever–when he hit town,” said Dingell. “And he had moved so fast, he never had any chance to grow scar tissue, to learn politics, to be hurt, because you’re going to be hurt in this business. Makes you tough, but you’ll learn. And so it’s a very important learning device, getting hurt.”

“He’s had to kind of fight his way up fast without the experience,” Dingell added. “His staff has, quite frankly, I think, tried to shelter him too much. And he hasn’t had the kitchen cabinet that he’s needed.”

We’ll have much more from Dingell’s interview with The Daily Rundown on Friday’s show and on the web.